Yes, I have reached successfully to destination 2018.3 from 10.1 with all the users, sites, workbooks intact.

But I am facing issues with live connections, Tableau server is unable to connect to the server ,i.e, Teradata, SQL Server and Postgre etc. Has anyone else faced the same issue? Do I need to reinstall the drivers? I believe I have lost all the drivers during the "Clean up". But the new set up should add all the drivers. Right?

My TS environments (which are on virtual servers) use two hard drives: One for the OS (C:) and the second for applications (D:) i.e. Tableau Server. Thus all of my drivers are installed in default locations on the C: drive so when I "blow away" TS it's only the D: drive that's affected, all of my drivers remain intact.

So, if all your drivers were on the same drive as TS and you wiped your TS clean then, yes, they are quite likely gone as well. The easy test would be to use Desktop on the actual TS to try to connect to those data sources. If Desktop connects then there's a TS issue; if you cannot connect with Desktop then the drivers need to be reinstalled.

I can't thank you enough Bryan. Thank you for taking the time to outline the process. I have been unable to upgrade for almost a year because of this issue. I have talked to Tableau at various times and they haven't been able to help. Finally today, Support found your note and relayed it to me. After a few hours, I got it upgraded!

A few small things that happened... my SSL certificate info didn't get restored. Probably because I had the SSL files in the Tableau directory I erased in the first step. That was easy to restore.

Also, I have an embedded dashboard in my website. The Trusted Authentication info was not restored. It took me a few minutes to figure that out.

I also missed step 4 in Part C. But the upgrade still worked without it.

Hi, I stumbled through upgrades from server version 10.5.1 to 2018.2.3 in our Dev and QA environments.

And ended up having to run the obliterate script to clear out all remnants and then do a fresh install and reload of content from Tableau backups.

I have been asking if Tableau could give the end user something like that obliterate script that users can run the first time they move from 10.X to 2018.2.

That would be okay as long as they verify their backup beforehand.

I am might consider doing your process as practice in Tableau Dev and see how it works- because I don't want to do 1 and an half upgrades/installs in Tableau server Prod.

BTW the main reason our upgrades failed were either explicit( fails right away, partial install and error messages) or implicit( could act as everything is good for a week and then on next reboot server becomes unlicensed) behind the scenes corruption of the Tableau licensing service.